


Betrayal and Bootleggers

by Bloopy42



Series: Living to Tell the Tale [2]
Category: Pirates of the Caribbean (Movies)
Genre: Action & Romance, Backstory, Canon Backstory, Canon Compliant, Denial of Feelings, Drabble, Drunken Flirting, Lost Love, Mutiny, Pirates, Prequel, Revenge, Slow Burn, Why is the Rum Gone?, marooning, swashbuckling
Language: English
Status: In-Progress
Published: 2020-09-09
Updated: 2020-09-09
Packaged: 2021-03-07 01:27:08
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence, Major Character Death
Chapters: 1
Words: 2,025
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26368669
Author URL: https://archiveofourown.org/users/Bloopy42/pseuds/Bloopy42
Summary: When Jack Sparrow was marooned on some godforsaken spit of land, he had no idea he'd be rescued a mere three days later by rum runners making their route. And among them, an old flame, no less...Just his luck.In a sorry and vengeful state, the fallen Captain must rely on old friends to pick him back up after officially hitting rock bottom.
Relationships: Hector Barbossa/Margaret Smyth, Jack Sparrow/Original Female Character(s)
Series: Living to Tell the Tale [2]
Series URL: https://archiveofourown.org/series/1916209
Kudos: 4





	Betrayal and Bootleggers

**Author's Note:**

> This fic has characters established in my backstory for Margaret Smyth, "Living To Tell The Tale". I recommend reading that first, but it can stand alone, too! Enjoy!

The waters that the creaking schooner cut through that cloudless day were the color of a gemstone Rita May had once seen, but could not name. She thought dully to herself, as she ran her dirty nails against a mast, that perhaps the transparent green-blue below had somehow been plucked and turned to treasure—as surely nothing on land could replicate that which belonged to the sea. It had to have been magic that captured the sea in a rock. If only she could remember what it had been called.

 _Magic…_ she shuddered when the word crossed her mind. A force she had hardly believed in years ago, even when her parents had been accused of practicing sorcery and taken from her as a young child. Her mother had mixed potions and prayed to the moon, but that was not magic nor fairytale—it was religion. Real magic was far more frightening, as she had learned not too long ago. Sea witches, enchanted trinkets, and bottled spells she would have scoffed at had she not seen them all with her own eyes. Many of her cohorts _did,_ when she regaled them with stories of her time on a certain infamous pirate ship. They didn’t have to believe her. She liked to tell the tales anyway, and at as many opportunities as she could, lest it begin to feel like a dream.

Yet ‘relief’ was not a strong enough word to describe how good it was to be back where she knew, on a rum-runner’s path. Rita was sent where she was needed, retrieving, delivering, or burying stashes to be sailed through ports of all kinds. As per the strict guidelines of the Smuggler’s Guild, all crews sent out followed particularly marked trajectories to avoid raids. The British navy that had colonized the Caribbean hardly bothered them, their questionably lawful operation of distributing goods and drink throughout the islands was harmless enough. Though, once in a while their checkpoints and inspections made making port rather difficult. Pirates were another monster entirely. Any decent Pirate could hardly resist a boatload of the finest ales. Trade Routes were created, sailed for a time, learned by those who listened, and then abandoned if deemed unsafe—meaning ships were suddenly being sunk. Rita, in her youthful and greedy state, couldn’t help but romanticize the pirate life. How thrilling to take what you want and give nothing back…

It wasn’t her, though. She lived too slowly when guilt weighed on her mind. Besides, she had expectations to live up to.

“I can see it, now,” came a voice behind her.

The rounded tip of a wooden spyglass poked out next to Rita’s head, and behind it was the squinting face of a young woman with freckled cheeks and curly jet hair, pulled back in a messy knot. Rita tried to act as though she’d not been spooked.

“’bout time,” She said, trying to peer at what the magnified eyes could make out in the distance. A wave sent the small ship jumping, and Rita lost her balance for an instant.

Margaret Smyth grabbed her arm to steady her, smirking as she lowered the spyglass.

“You’re off today, aren’t you?” Her friend asked. “Shall I tie you to the mast?”

“When they said the cache was in the middle of nowhere, I didn’t think they actually meant _the middle of nowhere_ ,” Rita muttered. She was sunburnt and her lips tasted of salt, neither of which she minded, but the physical tax did dampen her mood.

“You wouldn’t want Rumrunner’s Isle to be in the middle of everywhere, now would you?” Margret raised her eyebrows.

“I wouldn’t have named it such in the first place,” retorted Rita, but she moved over to the edge of the boat to look onto the horizon for a sign of land. Her friend came and stood beside her, close enough for whisper to be heard over the sound of the wake.

“I keep telling you, this isn’t punishment.”

Rita looked her in the eye, daring her to admit she was wrong. Margaret stared her down, however, and Rita huffed a long sigh.

“We haven’t been trusted with trips by our lonesome since….since, you know,” She muttered, gazing around at the few other sailors aboard. “We are assigned to serve in mediocre crews. We do nothing but go back and forth from cache to command post, carrying nothing more exciting than bloody ales.”

“World’s getting bigger, Rita,” Margaret said. “It can’t just be you and me in a dinghy hiding tobacco up our skirts anymore. If you haven’t noticed, we’ve gotten more work as of late. The business is expanding and we are adapting. And _we_ are trusted entirely to ensure everything goes to plan.”

“Then why aren’t _you_ at the helm?”

Both pairs of eyes darted across the deck to the ships small wooden wheel, behind which a portly man with a bandana was scratching his ear.

“He’s got experience,” shrugged Margaret.

“You’ve got talent,” Rita shot back. She shouldn’t have been so irritated over a tiny ship and an easy mission, but she couldn’t shake the feeling that she and her friend had only been looked down upon after their mistake of bringing pirates back to Smuggler’s Cove.

“I’m sorry this hasn’t been the excitement you’re used to,” Margaret narrowed her eyes. “But at least we’re safe. And employed. Captain Mulrogg,” She called off to the helmsman. He looked up, caught unawares. He was hardly a captain, but Margaret was adept at getting older men to fall to her whim with sheer flattery. “Sir, the Isle is up ahead on the starboard side.”

Sure enough, a spit of sand and trees were becoming less and less blurry.

“Aye, I see it!” Mulrogg called cheerily. “All hands make sails!

Before leaping to action, Margaret shot Rita a grin.

“We fetch the rum, and be home by nightfall to drink and dance until dawn. You can’t complain about that kind of life, can you?”

Rita returned the smile, before being struck with a word.

“Aquamarine,” She couldn’t help but say aloud as she tugged on a rope.

“What?”

“The water,” Rita was still smiling. “Looks like aquamarine.”

“I’ll buy you one when we make port,” Margaret seemed confused but laughed. “That way you can always remember this day.”

Rolling her eyes, Rita pulled her weight alongside the other men as they sped faster to the uncharted island. At least, uncharted by the rest of the world.

The schooner was small enough to pull through the shallows, up to the pure sandy coast, without getting caught on any reefs. It cut through the grains like a hot knife through butter, and halted to a perfect stop.

“’right, lads—and ladies,” Mulrogg pulled out a crowbar from behind one of the barrels lining the ship’s walls. “Stretch yer sea legs a wink. We’ll make this quick. Miss Smyth and I will start unloadin’ the wine n’ rum, while the rest of ye dig up the stash.”

He tossed Margaret the crowbar, which she snatched and used to lift open a crate of particularly desirable libations, each of which not yet made legal for trade in the Caribbean. The cellar on the island was loaded with bottles for their next delivery, and so began the simple task of replacing the sloshing liquids on the boat with the ones hidden below grass and sand.

Rita followed the three other men to a set of palm trees they must have known well, having made the journey before. Their hard boots changed tone once they hit buried wood. One young man named George took a gratuitous stomp on the terrain with a smile.

“Hear that, Miss May?” He winked at her. He had a wink that was quick as a flash and mystical to catch, like a falling star. Perhaps that was just the charm young men had when they were still full of hope. “The sound of hollow bellies about to be filled and empty pockets waiting to be filled, that is.”

“Don’t presume to be a poet, Banks,” Rita admonished playfully. She kicked at the sand where the men stood until the ground turned to plank. She bent down and felt for the latch, rusted from use and…

“Broken,” She muttered. “It’s been broken open.”

“It’s old,” one of the other men shrugged.

“This ain’t a populous route,” George added. “Likely wind and wear what tore the metal since human hands last touched it.”

Rita accepted the possibilities, and backed up to allow the men to pry up the cellar door. She quickly propped it open with the wooden stick resting against one of the palms.

“Down the hatch, boys,” she muttered, and they set to work. George climbed down first, and they listened for his creaking on the short steps to cease before peering in after him. Rita could make out his puzzled face, even shadowed in the dark. As the light spilled into the hole, she caught glimpses of sparkling on the bottom—unmistakably shards of broken glass.

“Half of it is…just gone,” George sounded as hollow as his steps had.

“Gone?” Rita followed him down and saw that he was right. The cobwebbed shelves were only partially lined with bottles of amber liquid, where they had once been overflowing. Underfoot crunched remnants of finished ales. Likely the culprit had not wasted a drop, rather smashed the dusty bottles to the ground once emptied. It was peculiar, but not unrecoverable. She shook her head.

“Someone might’ve passed through,” She concluded. “Take what we can, there’s still plenty. And start refilling the cellar with what’s on the ship. I very much doubt our little thief is still here.”

“Banks! May!” One of the men still on the surface was heard running back towards the cellar. He looked down at the two of them. “There’s a…” He gulped. “We’ve found a body.”

George and Rita exchanged a look, then scrambled to be the first one up the ladder.

“This ain’t the kind of thing a lady should see, eh?” Said the nervous man who had made the discovery. It was George who laughed.

“She can handle it,” He helped pull Rita out of the underground reserve. “She’s sailed with pirates, ‘member?”

Rita tried to ignore his teasing smile and looked ahead to where the man was pointing. In the shade of a fern that marked the beginning of a small cluster of flora, was the crooked shape of a human behind. It was flat on its back, and if been given a passing glance would haven blended all too well with its surroundings. A leather tricorne hat rested over his face, but it was distinguishably a male figure.

“He’s dead, poor soul,” said the sailor, shaking his head. “Probably left here for it.”

Rita stepped close enough to see the slow rise and fall of the dead man’s chest.

“He’s asleep,” She scoffed. “And he’s still got one of our bottles.”

Sure enough, like a beloved childhood toy, an open sloshing bottle of rum was tucked under his arm. George, bold as he pleased, marched over to the body and wrenched it from his clutch. That sent the sleeping man into a frenzy. He bolted upright, drawing his sword instantly and waving it at those within range. The hat fell off his face, revealing baggy, coal-like eyes. Rita froze. He looked much older than she remembered, sunken and on the brink of collapse, though it had not been so long since they had first met. No, there was no mistaking him. Unfortunately.

George had already drawn his pistol, followed closely by the other two men. Rita stood still, waiting for him to predictably try and talk his way out of the scenario. He looked around erratically, but his gaze fell fast on Rita and softened.

“Dearest, charming, girl,” Jack slurred. “I thought I might see you in death. Or is this a dream? Either way, far quicker and easier than I’d imagined.”

“Sparrow,” Rita felt the corners of her lips pull taut. “What have you got yourself into this time?”


End file.
